Product Name

  • Name

    Betamethasone 17,21-dipropionate

  • EINECS 227-005-2
  • CAS No. 5593-20-4
  • Article Data5
  • CAS DataBase
  • Density 1.24 g/cm3
  • Solubility
  • Melting Point 178 °C
  • Formula C28H37FO7
  • Boiling Point 603.2 °C at 760 mmHg
  • Molecular Weight 504.596
  • Flash Point 318.6 °C
  • Transport Information
  • Appearance Powder
  • Safety 22-24/25
  • Risk Codes
  • Molecular Structure Molecular Structure of 5593-20-4 (Betamethasone 17,21-dipropionate)
  • Hazard Symbols
  • Synonyms Pregna-1,4-diene-3,20-dione,9-fluoro-11b,17,21-trihydroxy-16b-methyl-, 17,21-dipropionate (7CI,8CI);Diproderm;Diprolene;Diprosis;Diprosone;Maxivate;Psorion;Rinderon DP;S3440;Sch 11460;b-Methasone 17,21-dipropionate;Halometasone Monohydrate;Pregna-1,4-diene-3,20-dione,9-fluoro-11-hydroxy-16-methyl-17,21-bis(1-oxopropoxy)-, (11b,16b)-;
  • PSA 106.97000
  • LogP 3.81750

Synthetic route

betamethasone
378-44-9

betamethasone

betamethasone dipropionate
5593-20-4

betamethasone dipropionate

Conditions
ConditionsYield
Multi-step reaction with 3 steps
1: toluene-4-sulfonic acid / tetrahydrofuran / 2 h / 15 - 20 °C / Inert atmosphere
2: aluminum (III) chloride / 16.5 h / 10 - 30 °C
3: tetrahydrofuran; water / 8 h / 50 - 80 °C / 450.05 Torr
View Scheme
Betamethasone propionate
5534-13-4

Betamethasone propionate

betamethasone dipropionate
5593-20-4

betamethasone dipropionate

Conditions
ConditionsYield
In tetrahydrofuran; water at 50 - 80℃; under 450.045 Torr; for 8h;
betamethasone dipropionate
5593-20-4

betamethasone dipropionate

17α,21-dihydroxy-9α-fluoro-16β-methylpregna-1,4,11(12)-triene-3,20-dione 17,21-dipropionate
65669-64-9

17α,21-dihydroxy-9α-fluoro-16β-methylpregna-1,4,11(12)-triene-3,20-dione 17,21-dipropionate

Conditions
ConditionsYield
With (diethylamido)sulfur trifluoride In dichloromethane for 16h; Ambient temperature;93%
P2 S5

P2 S5

betamethasone dipropionate
5593-20-4

betamethasone dipropionate

9α-Fluoro-16β-methyl-11,17,21-trihydroxypregna-1,4-dien-20-one-3-thione 17,21-dipropionate

9α-Fluoro-16β-methyl-11,17,21-trihydroxypregna-1,4-dien-20-one-3-thione 17,21-dipropionate

Conditions
ConditionsYield
In toluene60%
betamethasone dipropionate
5593-20-4

betamethasone dipropionate

9α-fluoro-6β,11β,17α,21-tetrahydroxy-16β-methyl-1,4-pregnadiene-3,20-dione 17,21-dipropionate
72559-81-0

9α-fluoro-6β,11β,17α,21-tetrahydroxy-16β-methyl-1,4-pregnadiene-3,20-dione 17,21-dipropionate

Conditions
ConditionsYield
With selenious acid In 1,4-dioxane at 100℃; for 72h;44.2%
With selenium(IV) oxide In 1,4-dioxane at 110℃; for 2.5h;25%
Multi-step reaction with 2 steps
1: pyridine / 18 h / 60 °C
2: oxygen / CHCl3 / 3 h
View Scheme
betamethasone dipropionate
5593-20-4

betamethasone dipropionate

A

betamethasone
378-44-9

betamethasone

B

Betamethasone propionate
5534-13-4

Betamethasone propionate

C

6β-hydroxybetamethasone
24703-00-2

6β-hydroxybetamethasone

D

6β-hydroxybetamethasone 17-propionate
78144-00-0

6β-hydroxybetamethasone 17-propionate

Conditions
ConditionsYield
With phosphate buffer; air; plasma of 20 d pregnant Sprague-Dawley rat at 37℃; for 1h; Product distribution; metabolism with tissues (plasma, liver, brain, placenta) from mothers and fetuses of Sprague-Dawley rats sacrificed on day 20 of pregnancy and mice on day 17 of pregnancy, further in vivo;A 14.8 % Chromat.
B 67.8 % Chromat.
C 1.4 % Chromat.
D 2.3 % Chromat.
...Expand
betamethasone dipropionate
5593-20-4

betamethasone dipropionate

Betamethasone propionate
5534-13-4

Betamethasone propionate

Conditions
ConditionsYield
With hydrogenchloride In ethanol for 6h; Ambient temperature;
betamethasone dipropionate
5593-20-4

betamethasone dipropionate

benzoyl chloride
98-88-4

benzoyl chloride

9α-fluoro-3,11β,17α,21-tetrahydroxy-16β-methyl-1,3,5-pregnatriene-20-one 3-benzoate 17,21-dipropionate
82926-64-5

9α-fluoro-3,11β,17α,21-tetrahydroxy-16β-methyl-1,3,5-pregnatriene-20-one 3-benzoate 17,21-dipropionate

Conditions
ConditionsYield
In pyridine at 60℃; for 18h;
betamethasone dipropionate
5593-20-4

betamethasone dipropionate

A

betamethasone
378-44-9

betamethasone

B

Betamethasone propionate
5534-13-4

Betamethasone propionate

C

betamethasone 21-monopropionate

betamethasone 21-monopropionate

Conditions
ConditionsYield
With sulfuric acid In acetonitrile at 20℃; for 20h; Product distribution; Further Variations:; Temperatures;
...Expand
betamethasone dipropionate
5593-20-4

betamethasone dipropionate

A

(Z)-betamethasone 20-hydroxy-17(20)-en-21-aldehyde

(Z)-betamethasone 20-hydroxy-17(20)-en-21-aldehyde

B

(E)-betamethasone 20-hydroxy-17(20)-en-21-aldehyde

(E)-betamethasone 20-hydroxy-17(20)-en-21-aldehyde

Conditions
ConditionsYield
With sodium hydroxide In acetonitrile at 20℃; for 0.333333h; Mattox rearrangement;A 30 % Chromat.
B 10 % Chromat.
With sodium hydroxide In water; acetonitrile at 20℃; for 0.333333h; Mattox rearrangement;
betamethasone dipropionate
5593-20-4

betamethasone dipropionate

9α-fluoro-11β,17α,21-trihydroxy-16β-methyl-1,4-pregnadiene-3,6,20-trione 17,21-dipropionate
72559-88-7

9α-fluoro-11β,17α,21-trihydroxy-16β-methyl-1,4-pregnadiene-3,6,20-trione 17,21-dipropionate

Conditions
ConditionsYield
Multi-step reaction with 3 steps
1: pyridine / 18 h / 60 °C
2: oxygen / CHCl3 / 3 h
3: 77 percent / pyridne/ CF3COOH/ 1-cyclohexyl-3-(2-morpholinoethyl) carbodiimide metho-p-toluenesulfonate / dimethylsulfoxide; benzene / 2 h / Ambient temperature
View Scheme
betamethasone dipropionate
5593-20-4

betamethasone dipropionate

9α-fluoro-6,11β,17α,21-tetrahydroxy-16β-methyl-1,4,6-pregnatriene-3,20-dione 6-acetate 17,21-dipropionate
72559-27-4

9α-fluoro-6,11β,17α,21-tetrahydroxy-16β-methyl-1,4,6-pregnatriene-3,20-dione 6-acetate 17,21-dipropionate

Conditions
ConditionsYield
Multi-step reaction with 4 steps
1: pyridine / 18 h / 60 °C
2: oxygen / CHCl3 / 3 h
3: 77 percent / pyridne/ CF3COOH/ 1-cyclohexyl-3-(2-morpholinoethyl) carbodiimide metho-p-toluenesulfonate / dimethylsulfoxide; benzene / 2 h / Ambient temperature
4: 51 percent / pyridine / 5 h / Ambient temperature
View Scheme
betamethasone dipropionate
5593-20-4

betamethasone dipropionate

9α-fluoro-6,11β,17α,21-tetrahydroxy-16β-methyl-1,4,6-pregnatriene-3,20-dione 6-isobutyrate 17,21-dipropionate
72559-99-0

9α-fluoro-6,11β,17α,21-tetrahydroxy-16β-methyl-1,4,6-pregnatriene-3,20-dione 6-isobutyrate 17,21-dipropionate

Conditions
ConditionsYield
Multi-step reaction with 4 steps
1: pyridine / 18 h / 60 °C
2: oxygen / CHCl3 / 3 h
3: 77 percent / pyridne/ CF3COOH/ 1-cyclohexyl-3-(2-morpholinoethyl) carbodiimide metho-p-toluenesulfonate / dimethylsulfoxide; benzene / 2 h / Ambient temperature
4: 63 percent / pyridine / 5 h / Ambient temperature
View Scheme
betamethasone dipropionate
5593-20-4

betamethasone dipropionate

9α-fluoro-6,11β,17α,21-tetrahydroxy-16β-methyl-1,4,6-pregnatriene-3,20-dione 6-valerate 17,21-dipropionate
72560-00-0

9α-fluoro-6,11β,17α,21-tetrahydroxy-16β-methyl-1,4,6-pregnatriene-3,20-dione 6-valerate 17,21-dipropionate

Conditions
ConditionsYield
Multi-step reaction with 4 steps
1: pyridine / 18 h / 60 °C
2: oxygen / CHCl3 / 3 h
3: 77 percent / pyridne/ CF3COOH/ 1-cyclohexyl-3-(2-morpholinoethyl) carbodiimide metho-p-toluenesulfonate / dimethylsulfoxide; benzene / 2 h / Ambient temperature
4: 58 percent / pyridine / 5 h / Ambient temperature
View Scheme
betamethasone dipropionate
5593-20-4

betamethasone dipropionate

9α-fluoro-6,11β,17α,21-tetrahydroxy-16β-methyl-1,4,6-pregnatriene-3,20-dione 6-trimethylacetate 17,21-dipropionate
72559-32-1

9α-fluoro-6,11β,17α,21-tetrahydroxy-16β-methyl-1,4,6-pregnatriene-3,20-dione 6-trimethylacetate 17,21-dipropionate

Conditions
ConditionsYield
Multi-step reaction with 4 steps
1: pyridine / 18 h / 60 °C
2: oxygen / CHCl3 / 3 h
3: 77 percent / pyridne/ CF3COOH/ 1-cyclohexyl-3-(2-morpholinoethyl) carbodiimide metho-p-toluenesulfonate / dimethylsulfoxide; benzene / 2 h / Ambient temperature
4: 56 percent / various solvent(s) / 5 h / Ambient temperature
View Scheme
betamethasone dipropionate
5593-20-4

betamethasone dipropionate

9α-fluoro-6,11β,17α,21-tetrahydroxy-16β-methyl-1,4,6-pregnatriene-3,20-dione 6-benzoate 17,21-dipropionate
72559-98-9

9α-fluoro-6,11β,17α,21-tetrahydroxy-16β-methyl-1,4,6-pregnatriene-3,20-dione 6-benzoate 17,21-dipropionate

Conditions
ConditionsYield
Multi-step reaction with 4 steps
1: pyridine / 18 h / 60 °C
2: oxygen / CHCl3 / 3 h
3: 77 percent / pyridne/ CF3COOH/ 1-cyclohexyl-3-(2-morpholinoethyl) carbodiimide metho-p-toluenesulfonate / dimethylsulfoxide; benzene / 2 h / Ambient temperature
4: 70 percent / pyridine / 5 h / Ambient temperature
View Scheme
betamethasone dipropionate
5593-20-4

betamethasone dipropionate

9α-fluoro-6,11β,17α,21-tetrahydroxy-16β-methyl-1,4,6-pregnatriene-3,20-dione 6-methanesulfonate 17,21-dipropionate
82934-60-9

9α-fluoro-6,11β,17α,21-tetrahydroxy-16β-methyl-1,4,6-pregnatriene-3,20-dione 6-methanesulfonate 17,21-dipropionate

Conditions
ConditionsYield
Multi-step reaction with 4 steps
1: pyridine / 18 h / 60 °C
2: oxygen / CHCl3 / 3 h
3: 77 percent / pyridne/ CF3COOH/ 1-cyclohexyl-3-(2-morpholinoethyl) carbodiimide metho-p-toluenesulfonate / dimethylsulfoxide; benzene / 2 h / Ambient temperature
4: 41 percent / pyridine / 5 h / Ambient temperature
View Scheme
betamethasone dipropionate
5593-20-4

betamethasone dipropionate

17α,21-dihydroxy-9α-fluoro-16β-methylpregna-1,4,11(12)-triene-3,20-dione
127034-59-7

17α,21-dihydroxy-9α-fluoro-16β-methylpregna-1,4,11(12)-triene-3,20-dione

Conditions
ConditionsYield
Multi-step reaction with 2 steps
1: 93 percent / (diethylamido)sulfur trifluoride (DAST) / CH2Cl2 / 16 h / Ambient temperature
2: 88 percent / NaHCO3 / methanol / 1 h / Heating
View Scheme
betamethasone dipropionate
5593-20-4

betamethasone dipropionate

16β-methyl-12β,17α,21-trihydroxypregna-1,4,9(11)-triene-3,20-dione
127034-60-0

16β-methyl-12β,17α,21-trihydroxypregna-1,4,9(11)-triene-3,20-dione

Conditions
ConditionsYield
Multi-step reaction with 3 steps
1: 93 percent / (diethylamido)sulfur trifluoride (DAST) / CH2Cl2 / 16 h / Ambient temperature
2: 88 percent / NaHCO3 / methanol / 1 h / Heating
3: 57 percent / 48percent aq. HF / 1.5 h / 22 °C
View Scheme
betamethasone dipropionate
5593-20-4

betamethasone dipropionate

16β-methyl-12α,17α,21-trihydroxypregna-1,4,9(11)-triene-3,20-dione
127034-61-1

16β-methyl-12α,17α,21-trihydroxypregna-1,4,9(11)-triene-3,20-dione

Conditions
ConditionsYield
Multi-step reaction with 3 steps
1: 93 percent / (diethylamido)sulfur trifluoride (DAST) / CH2Cl2 / 16 h / Ambient temperature
2: 88 percent / NaHCO3 / methanol / 1 h / Heating
3: 19 percent / 48percent aq. HF / 1.5 h / 22 °C
View Scheme
p-TSA hydrate

p-TSA hydrate

betamethasone dipropionate
5593-20-4

betamethasone dipropionate

9α-Fluoro-11β,17α,21-trihydroxy-16β-methyl-5β-pregnane-3,20-dione 17,21-dipropionate
80226-13-7

9α-Fluoro-11β,17α,21-trihydroxy-16β-methyl-5β-pregnane-3,20-dione 17,21-dipropionate

Conditions
ConditionsYield
palladium In dichloromethane; 4,4-dichlorobutan-2-one; acetone
palladium In dichloromethane; 4,4-dichlorobutan-2-one; acetone
betamethasone dipropionate
5593-20-4

betamethasone dipropionate

9α-Fluoro-16β-methyl-11,17-21-trihydroxypregna-1,4-dien-20-one-3-thione
64681-07-8

9α-Fluoro-16β-methyl-11,17-21-trihydroxypregna-1,4-dien-20-one-3-thione

Conditions
ConditionsYield
Multi-step reaction with 2 steps
1: toluene
2: sodium hydroxide; acetic acid / methanol
View Scheme

Betamethasone 17,21-dipropionate Chemical Properties


IUPAC Name: [2-[(8S,9R,10S,11S,13S,14S,16S,17R)-9-Fluoro-11-hydroxy-10,13,16-trimethyl-3-oxo-17-propanoyloxy-6,7,8,11,12,14,15,16-octahydrocyclopenta[a]phenanthren-17-yl]-2-oxoethyl] propanoate
Molecular Weight: 504.587583 [g/mol]
Molecular Formula: C28H37FO7
XLogP3: 3.6
H-Bond Donor: 1
H-Bond Acceptor: 8 
EINECS: 227-005-2
Product Categories: Biochemistry; Hydroxyketosteroids; Steroids 
refractive index: 69 °(C=1, Dioxane)
Water Solubility: 0.724 mg/L at 25 °C
Index of Refraction: 1.549
Molar Refractivity: 128.66 cm3
Molar Volume: 403.9 cm3
Surface Tension: 49.1 dyne/cm
Density: 1.24 g/cm3
Flash Point: 318.6 °C
Enthalpy of Vaporization: 102.93 kJ/mol
Boiling Point: 603.2 °C at 760 mmHg
Vapour Pressure: 4.58E-17 mmHg at 25 °C
Melting Point: 178 °C
Classification Code of Betamethasone dipropionate (CAS NO.5593-20-4): Anti-Inflammatory Agents; Drug / Therapeutic Agent; Glucocorticoid; Hormone; Reproductive Effect 

Betamethasone 17,21-dipropionate Uses

 Betamethasone dipropionate (CAS NO.5593-20-4) is applied as a topical cream, ointment, lotion or gel (Diprolene) to treat itching and other minor skin conditions such as eczema.

Betamethasone 17,21-dipropionate Toxicity Data With Reference

Organism Test Type Route Reported Dose (Normalized Dose) Effect Source
mouse LD50 intraperitoneal 103mg/kg (103mg/kg)   Drugs in Japan Vol. 6, Pg. 753, 1982.
mouse LD50 oral > 5gm/kg (5000mg/kg) BEHAVIORAL: ANTIPSYCHOTIC

SKIN AND APPENDAGES (SKIN): HAIR: OTHER		 Shikoku Igaku Zasshi. Shikoku Medical Journal. Vol. 29, Pg. 153, 1973.
mouse LD50 subcutaneous 78100ug/kg (78.1mg/kg)   Drugs in Japan Vol. 6, Pg. 753, 1982.
rat LD50 intraperitoneal > 4gm/kg (4000mg/kg)   Shikoku Igaku Zasshi. Shikoku Medical Journal. Vol. 29, Pg. 153, 1973.
rat LD50 oral > 4gm/kg (4000mg/kg)   Shikoku Igaku Zasshi. Shikoku Medical Journal. Vol. 29, Pg. 153, 1973.
rat LD50 subcutaneous > 4gm/kg (4000mg/kg)   Shikoku Igaku Zasshi. Shikoku Medical Journal. Vol. 29, Pg. 153, 1973.

Betamethasone 17,21-dipropionate Safety Profile

Safety Statements: 22-24/25
22:Do not breathe dust
24/25:Avoid contact with skin and eyes
WGK Germany: 2
RTECS: TU4058000
Poison by subcutaneous and intraperitoneal routes. An experimental teratogen. Other experimental reproductive effects. When heated to decomposition it emits toxic fumes of F−.

Betamethasone 17,21-dipropionate Specification

  Betamethasone dipropionate (CAS NO.5593-20-4), its Synonyms are 9-Fluoro-11beta,17,21-trihydroxy-16beta-methylpregna-1,4-diene-3,20-dione 17,21-dipropionate ; Alphatrex ; Betamethasone 17,21-dipropionate ; Diproderm ; Diprolene ; Diprolene AF ; Diprosis ; Diprosone ; Maxivate ; Psorion ; Rinderon DP ; beta-Methasone 17,21-dipropionate ; Pregna-1,4-diene-3,20-dione, 9-fluoro-11-beta,17,21-trihydroxy-16-beta-methyl-, 17,21-dipropionate ; Pregna-1,4-diene-3,20-dione, 9-fluoro-11-hydroxy-16-methyl-17,21-bis(1-oxopropoxy)-, (11beta,16beta) .

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